Recent results in studies of interactions between dopamine receptors and stereoselective agonists and antagonists are reviewed. Also discussed are the stereoselectivity of seotonergic 5-HT1A-receptor agonists and some of the difficulties associated with modeling the interaction between ligands and receptors on a molecular level
SmithDF, ed. CRC Handbook of Stereoisomers: drugs in psychopharmacology. Boca Raton, FL: CRC Press; 1984.
2.
DrayerDE. The early history of stereochemistry. In: WainerIWDrayerDE, eds. Drug stereochemistry: analytical methods and pharmacology. New York, NY: Marcel Dekker; 1988:3–29.
3.
HacksellUArvidssonL-ESvenssonUNilssonJLGSanchezDWikströmHLindbergPHjorthSCarlssonA. 3-Phenylpiperidines. Central dopamine-autoreceptor stimulating activity. J Med Chem.1981;24:1475–1482.
4.
HjorthSCarlssonAWikströmHLindbergPSanchezDHacksellUArvidssonL-ESvenssonUNilssonJLG. 3-PPP, A new centrally acting DA-receptor agonist with selectivity for autoreceptors. Life Sci.1981;28:1225–1238.
5.
WikströmHSanchezDLindbergPHacksellUArvidssonL-EJohanssonAMThorbergS-ONilssonJLGSvenssonKHjorthSClarkDCarlssonA. Resolved 3-(3-hydroxyphenyl)-N-n-propylpiperidine and its analogues: central dopamine receptor activity. J Med Chem.1984;27:1030–1036.
6.
HjorthSCarlssonAClarkDSvenssonKWikströmHSanchezDLindbergPHacksellUArvidssonL-EJohanssonANilssonJLG. Central dopamine receptor agonist and antagonist actions of the enantiomers of 3-PPP. Psychopharmacology. 1983;81:89–99.
7.
HjorthSClarkDCarlssonA. Dopamine (DA) autoreceptor efficacy of the 3-PPP enantiomers after short-term synaptic DA deprivation. Eur J Pharmacol. 1988;152:207–215.
8.
ClarkDHjorthSCarlssonA. Novel dopaminergic agents with selective autoreceptor agonist activity. I. Review of the evidence. J Neural Transm. 1985;62:1–52. 9.
9.
ClarkDHjorthSCarlssonA. Novel dopaminergic agents with selective autoreceptor agonist activity. II. Theoretical considerations. J Neural Transm. 1985;62:109–152.
10.
JohanssonAMArvidssonL-EHacksellUNilssonJLGSvenssonKHjorthSClarkDCarlssonASanchezDAnderssonBWikströmH. Novel dopamine receptor agonists and antagonists with preferential action on autoreceptors. J Med Chem.1985;28:1049–1053.
11.
JohanssonAMKarlénAGrolCSundellSKenneLHacksellU. Dopaminergic 2-aminotetralins: affinities for dopamine D2-receptors, molecular structures and conformational preferences. Mol Pharmacol. 1986;30:258–269.
12.
JohanssonAMArvidssonL-EHacksellUNilssonJLGSvenssonKCarlssonA. Resolved cis- and trans-2-amino-5-methoxy-1-tetralins: central dopamine receptor agonists and antagonists. J Med Chem.1987;30:602–611.
13.
JohanssonAMNilssonJLGKarlénAHacksellUSvenssonKCarlssonAKenneLSundellS. C3-Methylated 5-hydroxy-2-(dipropylamino)tetralins: conformational and steric parameters are of importance for central dopamine receptor activation. J Med Chem.1987;30:1135–1144.
14.
JohanssonAMNilssonJLGKarlénAHacksellUSanchezDSvenssonKHjorthSCarlssonASundellSKenneL. C1- And C3-methyl-substituted derivatives of 7-hydroxy-2-(di-n-propylamino)tetralin: activities at central dopamine receptors. J Med Chem.1987;30:1827–1837.
15.
McDermedJDFreemanHS. Stereochemistry of dopamine-receptor agonists. In: KohsakaMShohmoriTTsuhadaYWoodruffGN, eds. Advances in dopamine research. Oxford: Pergamon; 1981:179–187.
16.
KarlénAJohanssonAMKenneLArvidssonL-EHacksellU. Conformational analysis of the dopamine-receptor agonist 5-hydroxy-2-(dipropylamino)tetralin and its C(2)-methyl substituted derivative. J Med Chem.1986;29:917–924.
17.
SvenssonKHjorthSClarkDCarlssonAWikströmHAnderssonBSanchezDJohanssonAMArvidssonL-EHacksellUNilssonJLG. (+)-UH 232 and (+)-UH 242: novel stereoselective dopamine receptor antagonists with preferential action on autoreceptors. J Neural Transm. 1985;65:1–27.
18.
GrolCJNordvallGJohanssonAMHacksellU. 5-Oxygenated N-alkyl-2-amino-1-methyltetralins. Effects of structure and stereochemistry on dopamin D2-receptor affinity. Unpublished.
19.
KarlssonABjörkLPetterssonCAndénN-EHacksellU. (R)- And (S)-5-hydroxy-2-(dipropylamino)tetralin (5-OH DPAT): assessment of optical purities and dopaminergic activities. Chirality1990;2:90–95.
20.
AriensEJLehmanPADe MirandaRJF. Stereoselectivity and affinity in molecular pharmacology. Prog Drug Res.1976;20:101–142.
21.
ArvidssonL-EHacksellUSvenssonUNilssonJLGHjorthSCarlssonASanchezDLindbergPWikströmH. 8-Hydroxy-2-di-n-propylaminotetralin, a new centrally acting 5-HT-receptor agonist. J Med Chem.1981;24:921–923.
22.
HjorthSCarlssonALindbergPSanchezDWikströmHArvidssonL-EHacksellUNilssonJLG. 8-Hydroxy-2-(di-n-propylamino)tetralin, 8-OH DPAT, a potent and selective simplified ergot congener with central 5-HT-receptor stimulating activity. J Neural Transm. 1982;55:169–188.
23.
GozlanHEl MestikawySPichatLGlowinskyJHamonM. Identification of presynaptic serotonin autoreceptors using a new ligand: 3H-PAT. Nature, 1983;305:140–142.
24.
KarlssonAPetterssonCSundellSArvidssonN-EHacksellU. Improved separation, chromatographic separation and X-ray crystallographic determination of the absolute configuration of the enantiomers of 8-hydroxy-2-(dipropylamino) tetralin (8-OH DPAT). Acta Chem Scand. 1988;B42:231–236.
25.
BjörkLHöökBacklund BNelsonDLAndénL-EHacksellU. Resolved N, N-dialkylated 2-amino-8-hydroxytetralins: stereoselective interactions with 5-HT1A receptors in the brain. J Med Chem.1989;32:779–783.
26.
ArvidssonL-EJohanssonAMHacksellUNilssonJLGSvenssonKHjorthSMagnussonTCarlssonAAnderssonBWikströmH, (+)-cis-8-Hydroxy-1-methyl-2-(di-n-propylamino)tetralin: A potent and highly stereoselective 5-hydroxytryptamine receptor agonist. J Med Chem.1987;30:2105–2109.
27.
HjorthSSharpTHacksellU. Partial postsynaptic 5-HT1A agonist properties of the novel stereoselective 8-OH-DPAT analogue (+)-cis-8-hydroxy-1-methyl-2-(di-n-propylamino)tetralin, (+)-ALK-3. Eur J Pharmacol. 1989;170:269–274.
28.
ArvidssonL-EKarlénANorinderUKenneLSundellSHacksellU. Structural factors of importance for 5-hydroxytryptaminergic activity. Conformational preferences and electrostatic potentials of 8-hydroxy-2-(di-n-propylamino)tetralin (8-OH DPAT) and some related agents. J Med Chem.1988;31:212–221.
29.
MellinCBjörkLKarlénAJohanssonAMSundellSKenneLNelsonDLAndénN-EHacksellU. Central dopaminergic and 5-hydroxytryptaminergic effects of C3-methylated derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin. J Med Chem.1988;31:1130–1140.
30.
BjörkLMellinCHacksellUAndénN-E. Effects of the C3-methylated derivatives of 8-hydroxy-2-(di-n-propylamino)tetralin (8-OH-DPAT) on central 5-hydroxytryptaminergic receptors. Eur J Pharmacol. 1987;143:55–63.
31.
FarginARaymondJRLohseMJKoblikaBKCaronMGLefkowitzRJ. The genomic clone G-21 which resembles a β-adrenergic receptor sequence encodes the 5-HT1A receptor. Nature. 1988;335:358–360.
32.
DixonRAStraderCDSigalIS. Structure and function of G-protein coupled receptors. Ann Rep Med Chem.1988;23:221–233.
